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Ag-Catalyzed cycloisomerization of 1,6-enynamide: an intramolecular type II Alder-ene reaction

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Abstract

Promoted by a silver catalyst, 1,6-enynamides with a cyclic ene moiety can undergo cycloisomerization to fused N-heterobicycles. This transformation presents an unusual type II Alder-ene reaction and is believed to proceed through a catalytic cycle of formation of a keteneiminium silver intermediate, subsequent 6-endo-trig cyclization and protodemetalation.

Graphical abstract: Ag-Catalyzed cycloisomerization of 1,6-enynamide: an intramolecular type II Alder-ene reaction

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Publication details

The article was received on 14 Oct 2019, accepted on 14 Nov 2019 and first published on 18 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01258C
Org. Chem. Front., 2020, Advance Article

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    Ag-Catalyzed cycloisomerization of 1,6-enynamide: an intramolecular type II Alder-ene reaction

    M. Shen, Y. Zhang, C. Jiang, H. Xu and D. Xu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01258C

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